Hydrochloric Acid → 3-Bromoacetyloxymethyl-5,5-diphenyl-2,4-imidazolidinedione

HRID 703709Notes

Reaction equation

[C:1]1([C:7]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:11][C:10](=[O:12])[N:9]([CH2:13][OH:14])[C:8]2=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:22][CH2:23][C:24](Cl)=[O:25].Cl>C(OCC)C>[Br:22][CH2:23][C:24]([O:14][CH2:13][N:9]1[C:8](=[O:15])[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:11][C:10]1=[O:12])=[O:25]

Participants

Conditions

Temperature: 0 °C

Procedure

5,5-Diphenyl-3-hydroxymethyl-2,4-imidazolidinedione (2 g, 0.0071 mol) was dissolved in bromoacetylchloride (15 g, 8 mL, 0.096 mol) by heating in an oil bath (70°-80° C. bath temperature) for about 15 minutes, until the formation of HCl ceased. The mixture was cooled and 30 mL of ethyl ether were added. White crystals formed. The mixture was cooled to 0° C., then the crystals were removed by filtration and dried over P2O5. Yield: 2.15 g (75%), m.p. 179°-183° C. Anal. calc. for C18H15N2O4Br: C, 53.61, H, 3.75; N, 6.95; Br, 19.82. Found: C, 53.60; H, 3.79; N, 6.92; Br, 19.90. The product had the formula: ##STR74##

Workup

temperatureby heating in an oil bath (70°-80° C. bath temperature) for about 15 minutes
temperatureThe mixture was cooled
customWhite crystals formed
customthe crystals were removed by filtration
dry with materialdried over P2O5

Sources & evidence

ORD record: ord-c2612b0cee3a4edf99dca6127bcb565b
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04983586

Reaction notes

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